Glycine → HCID 24757242, compound

HRID 642326Notes

Reaction equation

HRID 642326 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[S:14][C:8]=2[C:7]=1[OH:21])=[O:5])C.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].C[O-].[Na+].CO>>[OH:21][C:7]1[C:8]2[S:14][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:12][C:9]=2[CH:10]=[N:11][C:6]=1[C:4]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:5]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 68427909HCID 68427909, compound

Product 1

HCID 24757242HCID 24757242, compoundYield 75.7%

Procedure

A mixture of 7-hydroxy-2-pyridin-2-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (43 mg, 0.14 mmol) and glycine (214 mg, 2.86 mmol) in 0.5 M sodium methoxide/methanol (5.4 mL, 1.29 mmol) was refluxed for 2 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water and extracted with methyl tert-butyl ether (2×25 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (4 mL). The precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (35 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.16 (br s, 1H), 9.47 (br s, 1H), 8.92 (s, 1H), 8.75 (d, J=4.3 Hz, 1H), 8.32 (d, J=7.8, 1H), 8.05 (m, 1H), 7.65 (m, 1H), 4.03 (d, J=6.3 Hz, 2H); MS: (+) m/z 331.00 (M+1); (−) m/z 329.00 (M−1).

Workup

  1. temperaturewas refluxed for 2 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with methyl tert-butyl ether (2×25 mL)
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1c2789129678434db326dc298b039196
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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